#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012323.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2012323
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  1326
_journal_page_last  1329
_publ_section_title
;
Diels-Alder adducts of medium-ring carbocyclic dienes prepared by
rearrangement of catalytically generated cyclic oxonium ylides
;
loop_
_publ_author_name
  'Wilson, Claire'
  'Clark, J. Stephen'
  'Bate, Andrea L.'
  'Blake, Alexander J.'
  'Grinter, Trevor'
  'Teat, Simon J.'
_chemical_formula_moiety  'C15 H20 O6'
_chemical_formula_sum  'C15 H20 O6'
_chemical_formula_iupac  'C15 H20 O6'
_chemical_formula_weight  296.31
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P b c a'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  '-x, y+1/2, -z+1/2'
  'x+1/2, -y+1/2, -z'
  '-x, -y, -z'
  'x-1/2, y, -z-1/2'
  'x, -y-1/2, z-1/2'
  '-x-1/2, y-1/2, z'
_cell_length_a  14.676(2)
_cell_length_b  9.967(2)
_cell_length_c  18.937(3)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  2770.0(8)
_cell_formula_units_Z  8
_cell_measurement_temperature  150(2)
_exptl_crystal_density_diffrn  1.421
_diffrn_ambient_temperature  150(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  C1  .0734(2)  .8207(3)  .69360(17)  .0230(8) Uani d . 1 . . C
  H1  .0091  .8484  .7030  .028 Uiso calc R 1 . . H
  C2  .1182(2)  .9317(4)  .65095(18)  .0264(8) Uani d . 1 . . C
  H2  .1138 1.0150  .6802  .032 Uiso calc R 1 . . H
  C3  .2209(2)  .9072(4)  .6379(2)  .0319(9) Uani d . 1 . . C
  H3A  .2286  .8571  .5931  .038 Uiso calc R 1 . . H
  H3B  .2521  .9947  .6326  .038 Uiso calc R 1 . . H
  C4  .2649(3)  .8303(4)  .6964(2)  .0347(10) Uani d . 1 . . C
  H4  .3283  .8130  .6917  .042 Uiso calc R 1 . . H
  C4a  .2247(2)  .7834(4)  .75456(19)  .0291(9) Uani d . 1 . . C
  C5  .2813(3)  .7076(4)  .8080(2)  .0355(10) Uani d . 1 . . C
  H5A  .3404  .6851  .7858  .043 Uiso calc R 1 . . H
  H5B  .2499  .6220  .8185  .043 Uiso calc R 1 . . H
  C6  .3006(3)  .7775(5)  .8774(2)  .0353(10) Uani d . 1 . . C
  H6A  .3115  .8737  .8675  .042 Uiso calc R 1 . . H
  H6B  .3577  .7402  .8971  .042 Uiso calc R 1 . . H
  C7  .2260(3)  .7670(5)  .9343(2)  .0346(10) Uani d . 1 . . C
  H7A  .2080  .6718  .9396  .042 Uiso calc R 1 . . H
  H7B  .2512  .7976  .9800  .042 Uiso calc R 1 . . H
  C8  .1430(3)  .8488(4)  .91697(17)  .0269(8) Uani d . 1 . . C
  O8  .1430(2)  .9700(3)  .92010(13)  .0369(7) Uani d . 1 . . O
  C9  .0597(2)  .7717(4)  .89150(18)  .0275(8) Uani d . 1 . . C
  H9  .0472  .6969  .9254  .033 Uiso calc R 1 . . H
  O9  -.01852(17)  .8565(3)  .88839(13)  .0312(7) Uani d . 1 . . O
  C9M  -.0651(3)  .8631(4)  .95555(19)  .0344(9) Uani d . 1 . . C
  H9M1  -.1181  .9224  .9515  .052 Uiso calc R 1 . . H
  H9M2  -.0235  .8982  .9915  .052 Uiso calc R 1 . . H
  H9M3  -.0854  .7730  .9692  .052 Uiso calc R 1 . . H
  C10  .0754(3)  .7122(4)  .81838(18)  .0271(8) Uani d . 1 . . C
  H10A  .0159  .6851  .7983  .033 Uiso calc R 1 . . H
  H10B  .1131  .6303  .8232  .033 Uiso calc R 1 . . H
  C10a  .1227(2)  .8084(4)  .76623(17)  .0232(8) Uani d . 1 . . C
  H10C  .1184  .8994  .7883  .028 Uiso calc R 1 . . H
  C11  .0704(2)  .6916(4)  .65070(18)  .0254(8) Uani d . 1 . . C
  O11  .0998(2)  .6811(3)  .59198(14)  .0397(7) Uani d . 1 . . O
  O12  .0266(2)  .5920(3)  .68351(15)  .0431(8) Uani d . 1 . . O
  H12  .0220  .5261  .6561  .065 Uiso calc R 1 . . H
  C21  .0674(3)  .9599(4)  .58358(18)  .0278(8) Uani d . 1 . . C
  O21  -.01638(18)  .9402(3)  .58095(14)  .0363(7) Uani d . 1 . . O
  O22  .11397(19) 1.0089(3)  .53182(13)  .0376(7) Uani d . 1 . . O
  H22  .0791 1.0245  .4976  .056 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  C1  .0146(16)  .032(2)  .0221(17)  .0015(15)  -.0015(13)  -.0038(14)
  C2  .0232(19)  .035(2)  .0212(17)  .0019(16)  -.0003(14)  -.0035(14)
  C3  .0206(19)  .049(3)  .0264(19)  -.0043(17)  -.0004(15)  .0040(17)
  C4  .0162(18)  .055(3)  .033(2)  -.0004(18)  .0018(15)  .0031(18)
  C4a  .0206(18)  .039(2)  .0281(19)  -.0002(16)  -.0008(15)  -.0003(16)
  C5  .0169(18)  .052(3)  .038(2)  .0092(18)  .0011(16)  .0073(18)
  C6  .023(2)  .051(3)  .032(2)  .0015(18)  -.0072(16)  .0084(18)
  C7  .031(2)  .049(2)  .0237(18)  -.0066(19)  -.0055(16)  .0107(17)
  C8  .031(2)  .036(2)  .0131(16)  -.0027(16)  .0043(14)  -.0032(14)
  O8  .0394(17)  .0408(19)  .0304(14)  -.0066(13)  .0042(12)  -.0054(12)
  C9  .0218(18)  .036(2)  .0250(18)  .0003(16)  .0047(14)  .0027(15)
  O9  .0253(14)  .0441(16)  .0240(13)  .0061(12)  .0036(10)  .0047(11)
  C9M  .028(2)  .048(2)  .0271(19)  .0000(19)  .0097(16)  .0030(17)
  C10  .0247(18)  .033(2)  .0233(17)  -.0033(16)  .0012(14)  -.0007(14)
  C10a  .0202(17)  .0314(19)  .0180(16)  -.0036(15)  -.0021(13)  -.0028(13)
  C11  .0184(17)  .035(2)  .0230(18)  .0000(16)  -.0054(14)  -.0040(15)
  O11  .0438(17)  .0438(17)  .0314(15)  -.0048(14)  .0123(13)  -.0094(12)
  O12  .056(2)  .0425(18)  .0309(15)  -.0190(15)  .0089(14)  -.0112(12)
  C21  .026(2)  .033(2)  .0249(18)  .0011(16)  .0018(15)  -.0047(15)
  O21  .0254(15)  .0487(18)  .0348(15)  .0000(12)  -.0026(11)  .0043(12)
  O22  .0335(15)  .0551(18)  .0243(13)  .0004(14)  -.0010(11)  .0096(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  C1 C2 . 1.520(5) ?
  C1 C11 . 1.522(5) ?
  C1 C10a . 1.559(4) ?
  C1 H1 . 1.000 ?
  C2 C21 . 1.504(5) ?
  C2 C3 . 1.547(5) ?
  C2 H2 . 1.000 ?
  C3 C4 . 1.494(5) ?
  C3 H3A .  .990 ?
  C3 H3B .  .990 ?
  C4 C4a . 1.335(5) ?
  C4 H4 .  .950 ?
  C4a C5 . 1.512(5) ?
  C4a C10a . 1.533(5) ?
  C5 C6 . 1.513(6) ?
  C5 H5A .  .990 ?
  C5 H5B .  .990 ?
  C6 C7 . 1.540(6) ?
  C6 H6A .  .990 ?
  C6 H6B .  .990 ?
  C7 C8 . 1.502(6) ?
  C7 H7A .  .990 ?
  C7 H7B .  .990 ?
  C8 O8 . 1.210(5) ?
  C8 C9 . 1.523(5) ?
  C9 O9 . 1.427(4) ?
  C9 C10 . 1.524(5) ?
  C9 H9 . 1.000 ?
  O9 C9M . 1.445(4) ?
  C9M H9M1 .  .980 ?
  C9M H9M2 .  .980 ?
  C9M H9M3 .  .980 ?
  C10 C10a . 1.541(5) ?
  C10 H10A .  .990 ?
  C10 H10B .  .990 ?
  C10a H10C . 1.000 ?
  C11 O11 . 1.197(4) ?
  C11 O12 . 1.336(5) ?
  O12 H12 .  .840 ?
  C21 O21 . 1.247(5) ?
  C21 O22 . 1.291(4) ?
  O22 H22 .  .840 ?